After eight years at Entertainment Weekly, where he "had gotten to do almost everything," Jay Woodruff jumped at the chance when Kent Brownridge asked him to head Maxim.com. (After all, as the former EW.com managing editor says, one can only "feign interest in American Idol for so long.") "Dr. Evil" left for OK! almost as soon as Woodruff arrived, but the editor continues to work with Maxim editorial director James Kaminsky building the site's content. (He also oversees Blender.com and StuffMagazine.com.) In October, Woodruff spoke with mediabistro.com about redesigning Maxim.com, filtering the news of the day through the Maxim voice, and why he doesn't have to worry about monetization.

Name: Jay Woodruff Position: Editor-in-chief, Maxim Digital, Alpha Media GroupResume: "After graduating from the second best college in Cambridge, Massachusetts, I took a job selling college textbooks for Prentice Hall where I spent less time selling college textbooks and more time writing stories and freelance articles. Before they could figure this out and fire me, I applied to the Iowa Writers Workshop, where I spent the next two years playing softball and trying to convince the cute girl on the first floor of my apartment building to go out with me. I left Iowa with an MFA, a couple of softball trophies, and a fiancée. (Married 20 years. Extravagant gifts welcome.) I spent the next four years as a research and teaching fellow at Harvard for Dr. Robert Coles and writing short stories that were published mainly in quarterlies that no longer exist. When Dr. Coles and Alex Harris decided to start a magazine, they hired me to help, and the result was DoubleTake. DoubleTake led to Esquire, Esquire to Entertainment Weekly. EW EIC Rick Tetzeli offered me the chance to move over to EW.com, which led eventually to my current job as EIC of Maxim Digital. Here's hoping this Internet thing will be really big." Birth date: "October 31, 1902."Hometown: Webster Groves, MissouriFirst section of the Sunday Times: Real EstateFavorite TV show:Mad Men, 30 Rock, The Daily Show, The Colbert Report, UFC, college football. Sopranos, Band of Brothers, and BBC's The Office on DVD.Last book read: "Our Story Begins, by Tobias Wolff, my favorite short story writer; just started The Snowball, Alice Schroeder's biography of Warren Buffett. I've decided I might like to become a billionaire and hope that this book offers some helpful tips."Guilty pleasure: Anything with sugar in it.

You've been at Maxim.com about four months now. How's it going? Is it different than you expected?
No, you know, it's great. I'm very happy to be here. I had been at Entertainment Weekly for eight years, so I was ready for a change. I loved Entertainment Weekly, had a great experience there, but that's a long time, you know? I was looking forward to being at a smaller organization, because I think we have the potential to be a little bit more nimble. And also my tastes are very eclectic when it comes to entertainment, and I'm not an entertainment omnivore, so I can only feign interest in American Idol for so long. Now I no longer have to pretend I'm interested at all.

I'm sure you've heard the golden age of the lad magazine is over. Maxim has tried to move away from that title, but where in the current marketplace does Maxim, and Maxim.com, fit?
I think that the labels that you apply to different magazines may come in and out of fashion. But I think it's still basically the same competitive set. I mean, there are some titles that have disappeared, but we're competing with GQ, Esquire, Details, ESPN, and the other titles that are demanding the attention of readers in our demo, 18 to 34. And the same sort of thing online, where almost every month there's a new site that's emerging and data that is going to be trying to draw attention from that same demographic. We compete with AskMen, with Heavy, with Break, and with some of the gaming sites.

The golden age of the lad magazine may be over, but there's still a lot of guys, and they're still looking for stuff to do, and they're still interested in looking at attractive women, and they're still interested in laughing. So we're still trying to feed that beast.

"The era of just simply repurposing magazine content online is long past. You bore your users online, and you wind up undermining the premium value of the print entity of the brand."

Where are you getting content for the site? A lot of the magazine's online, but in addition to stuff that's in the magazine, how big is the editorial staff on the dot-com side?
Well, the dot-com staff is right now about a dozen people. It has fluctuated between 12 and 18, but I think the natural level for us is 12 to 15 people, so we get most of our content from them. They're not all editors and writers. We have a designer and we have photo editors and we have two video editors. We also use some freelancers. We don't have a huge freelance budget, and I try to reserve as much of that as possible for freelance editors when we get into crunch periods where we really have to produce a lot of content. One of the things that Jim Kaminsky and I are working on together is trying to integrate more seamlessly with the magazine, so that we're getting more contributions from Maxim's editors.

One thing that works online is to bulk up a feature that's in the magazine with Web-only content. Is that something you're trying to do as well?
Yeah, the era of just simply repurposing magazine content online is long past. You bore your users online, and you wind up undermining the premium value of the print entity of the brand too if you do that too much.

We can run video, so when we have a cover shoot or a photo shoot and we usually have exclusive behind-the-scenes video of the shoot. We can run that. And we can also do offshoots. The next issue's going to have a feature on Oliver Stone. So we can do a slideshow or an article online that places W. within the context of other political movies, you know, stuff like that. Sidebar stuff works really well for us online.

That said, one of the advantages of being affiliated with a print entity is that the top magazines are produced by some of the best content creators in the world, and some of our most successful pieces are not just simply repurposed, but sort of reinvented, repackaged to work really effectively online. For example, we can turn a feature into a gallery or a slideshow, or just take it in a different direction. As we move along, our site is becoming more interactive and we're going to have a different set of tools where we can do more with games and just play with the content in new ways.

Kent Brownridge is gone now, but can you talk a little bit about what his role was when he was here, and sort of how things have changed now that Steve [Duggan] and Glenn [Rosenbloom] are on top?
Well, Kent hired me. So, I'm always going to be grateful to him for that. We only overlapped for a couple of months. And I think he was the point person leading the charge in trying to help the magazine and the Web site become more fully integrated and leverage one another more effectively. And Glenn and Stephen are doing exactly [that] -- they have the exact same goal now. I'm just reporting to a different general.

Any truth to the Dr. Evil name?
(Laughs) Not in my experience. No.

Can you just talk a little bit about the timing of you leaving EW.com? Cyndi Stivers took over as ME of EW.com soon before you left.
Yeah, I had gotten a call from Maxim, and I think I had had one, maybe two conversations with the headhunter, Karen Danziger, and then with Kent. At that point I'd been at EW for almost eight years. I had been doing the Web site for two and a half, and I was feeling a little burned out on entertainment and just wanted a change. When Karen called me I thought, sure, I'll talk -- you know, it never hurts to talk to people when you get those kinds of calls.

Rick Tetzeli had come to me several months before and asked me whether at some point I would be willing to come back to the magazine. My response was, 'I would definitely consider coming back to the magazine, but I don't want to do it right now because there's just too much unfinished business and there's a lot of stuff that I really want to see through.' And he agreed. So when he came to me and said he wanted me to come back and wanted Cyndi to come over -- first of all, I thought she was a great hire, and she and I didn't overlap much. I didn't work with her too much, but I really liked her and was very impressed by her. But at that point I still wasn't ready to come back to print.

Any reason why? Is it print specifically, or EW specifically?
Well, I had gotten to do almost everything at EW. I started out as a section editor in the back of the book, the movie review section, and then was promoted to AME, and oversaw the redesign of the front of the book. Then I managed the mix and the features well and I did bonus features, and then oversaw all the movie coverage. So I'd done front of the book, I'd done back of the book, I'd done features well, and I wasn't too excited about going back to doing a job I'd already done, you know?

So it was specifically not wanting to go back to do work that felt familiar to me, but also I love online. It's a new medium, it's changing constantly. The medium itself is changing, and the tools that we have to play with are changing. The business is also rapidly evolving. It's exciting. It's never boring. Sometimes it's frustrating. It's often exhausting. It's occasionally terrifying, but it's never boring.

One of the things you did at EW.com was redesign the site, and that was a huge success. How does that inform your experience coming over to Maxim.com? Is there a redesign in the future?
I've tried to make a few simple tweaks. And we're actually going to be unveiling some slightly more ambitious redesigns in the next week or two, redesigning the homepage, redesigning our key landing pages. Redesigns are very complicated and challenging. An editor can redesign an entire magazine six times in the amount of time it takes someone online to do a really good, holistic wholesale redesign of the site, because every change you make has architectural implications for the rest of the site.

"Hopefully advertisers will continue to want to be part of the Maxim party. My job is to try to make sure that we're creating the most engaging environment so that people here who are much smarter than I will ever be about money can figure out how they monetize some of it."

The last five percent of a redesign always seems to take just a shockingly long time.
Yeah, so you have to be very, very conscious of your available resources, the additional demands you're placing on those resources while you're doing the redesign, because you have to continue to operate the site effectively while you're doing the redesign. It can hurt you to be a little bit impetuous redesigning a Web site.

I think one of the smartest things Rick Tetzeli did at EW was introduce "The Must List." The first iteration of that that was published had no photos. The next week it looked completely different, had photos and looked pretty much exactly the way it looked for the next number of years, until they recently redesigned it again. It's hard to move that quickly online, and mistakes have different kinds of repercussions. So you have to be a little bit more thoughtful and careful, and therefore it takes a little bit longer, and that can be kind of frustrating for someone who has been in the print medium too.

Kent Brownridge mentioned that there were five million unique visitors across Maxim.com, Blender.com and StuffMagazine.com when you came over. Has traffic been increasing?
Yeah, traffic is picking up a little bit. If you're looking at the three combined we're between five and six million a month, and probably between 50 and 60 million page views a month on average. But, you know, my strategy is pretty simple, so simple that it may sound really stupid, but it worked at EW.com and I'm trying to apply it here, and that is simply to produce more content that is spot on for your demo and that is engaging, and make sure that you're working with designs that allow you to really showcase that and leverage that most effectively. And, you know, the more content you produce, the more opportunities you're going to have to strike syndication deals, partnership opportunities. There's no silver bullet.

Right.
At least I don't know of one. It's sort of a combination of more really good content, updating the sites frequently so that people have a reason to come back repeatedly, content that's going to appeal to partners so that you're creating some partnerships and a lot of cross-linking, making sure you're being smart about SEOs so that your stuff is popping in search. I mean it's kind of basic.

You make it sound simple. So where does the money come from?
Again, I think the economics of this medium are evolving pretty rapidly. And, you know, I think some people have a tendency to view the Web as this sort of magical, perpetual motion efficiency machine. There's no paper, there's no postage, so, it's, "God, it's basically free." Well, actually there are servers and there's a tech platform that has to be maintained, and there are actually people like me that have to create the content. So fortunately my job is mainly to try to create good content, and worry a little bit less about how that's going to be monetized. But, there's a correlation between content and traffic, and there's a correlation between traffic and how you get monetized. So there are sites out there that offer reach and there are sites out there that offer something else. And that's where I think sites like ours that feature an established, meaningful brand have some advantage. Presumably, hopefully advertisers will continue to want to be part of the Maxim environment, the Maxim experience, the Maxim party. And my job is to try to make sure that we're creating the most engaging environment so that people here who are much smarter than I will ever be about money can figure out how they monetize some of it.

Twelve months down the road where do you want to see the site?
Twelve months down the road I want the site to be much cleaner visually and to be offering between 20 and 30 items a day that allow us to refract whatever's going on in the world through the Maxim lens. I want us to be offering news for guys, you know? There's a lot going on in the world today. There's always a lot going on in the world, and we ought to be able to refract that.

I spend a lot of time thinking about The Daily Show, and what Jon Stewart did with that show when he showed up. I mean the show was always good. But he took it to a whole different level through humor. You know, he's provocative, he's smart. I want Maxim.com to be a really funny, smart destination for men that's also incredibly sexy. And I want us to be displaying our content on an absolutely state of the art platform, so we can leverage more than just pictures and text, but also the video more effectively, interactive games, everything. I want us to be able to fully exploit the medium that we're operating on.